Hydrochloric Acid → HCID 86635465, compound

HRID 2261791Notes

Reaction equation

HRID 2261791 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[CH3:15])[CH3:7])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:24][C:25]1[N:29]([C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:37])[N:28]=[CH:27][C:26]=1[CH:38]([CH3:40])[CH3:39].Cl>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:24][C:25]2[N:29]([C:30]3[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:37])[N:28]=[CH:27][C:26]=2[CH:38]([CH3:40])[CH3:39])=[CH:10][C:9]=1[CH3:15])[CH3:7])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 67529447HCID 67529447, compoundHCID 86635466HCID 86635466, compound

Product 1

HCID 86635465HCID 86635465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (+/−)-3-(4-Hydroxy-2-methyl-phenyl)-butyric acid ethyl ester (0.366 g, 0.748 mmol) in DMF (4 mL) is added cesium carbonate (1.1 g, 1.5 mmol). After 5 minutes at room temperature, 5-Chloromethyl-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-pyrazole (0.50 g, 0.748 mmol) is added and the reaction is heated to 50° C. overnight. Upon cooling, water is added followed by 1N HCl. The resulting mixture is extracted two times with ethyl acetate and the organic layers are combined and are washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified via flash chromatography eluting with 3-5% ethyl acetate/toluene to give the title compound. 1H NMR (CDCl3) δ 1.113-1.163 (m, 6H), 1.26 (d, 6H), 2.399-2.532 (m, 2H), 2.952 (m, 1H), 3.388 (m, 1H), 4.024 (q, 2H), 4.741 (s, 2H), 6.513 (d, 1H), 6.544 (dd, 1H), 6.970 (d, 1H), 7.264 (t, 1H), 7.372 (d, 2H), 7.661 (s, 1H)

Workup

  1. temperatureUpon cooling
  2. extractionThe resulting mixture is extracted two times with ethyl acetate
  3. washare washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified via flash chromatography
  8. washeluting with 3-5% ethyl acetate/toluene

Sources & evidence

ORD record
ord-4f573d4b04e54ecd96f294154d04990e
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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